Isoamyl Nitrite → HCID 131711529, compound

Temperature

-70 °C

pGlu-Ala-Lys(Xys)-Ser(Bzl)-Gln-Gly-Gly-NHNH2 (140 mg) is dissolved in dimethylformamide (5 ml). While the solution is cooled to -70° C., 6.51 N HCl-dioxane (0.05 ml) and isoamylnitrite (0.02 ml) are added. The mixture is stirred at -30° C. for 35 minutes and cooled again to -70° C., followed by addition of triethylamine (0.05 ml). HCl-H-Ser-Asn-OBut which is prepared by reducing Z-Ser-Asn-OBut (123 mg) is dissolved in dimethylformamide (2 ml) and this solution is added to the mixture, followed by addition of triethylamine (0.05 ml). The mixture is stirred between -15° C. and 5° C. for 30 hours. Insolubles are filtered off and the filtrate is distilled to evaporate the solvent. Ether is added and resulting powder is collected by filtration. Into a mixture of the powder and anisole contained in a cylinder of teflon resin, is introduced hydrogen fluoride (5 ml) and the mixture is stirred at 0° C. for one hour. Immediately the hydrogen fluoride is distilled off under reduced pressure and the residue is extracted twice-with water (10 ml each). The aqueous extract is washed three times with ether (3 ml each) and passed through a column (1.5×10 cm) of Amberlite IRA-410 (acetate form).

1. temperaturecooled again to -70° C.
2. additionthis solution is added to the mixture
3. stirringThe mixture is stirred between -15° C. and 5° C. for 30 hours
4. filtrationInsolubles are filtered off
5. distillationthe filtrate is distilled
6. customto evaporate the solvent
7. additionEther is added
8. customresulting powder
9. filtrationis collected by filtration
10. additionInto a mixture of the powder and anisole
11. additionis introduced hydrogen fluoride (5 ml)
12. stirringthe mixture is stirred at 0° C. for one hour
13. distillationImmediately the hydrogen fluoride is distilled off under reduced pressure
14. extractionthe residue is extracted twice-with water (10 ml each)
15. extractionThe aqueous extract
16. washis washed three times with ether (3 ml each)

ORD record

ord-a536900534274d988b2667f1248acfd5

Source dataset

uspto-grants-1979_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04159979